How to break your sales goals while taking a vacation

Records are meant for breaking. 9 months ago, I promised to make the most impact where I knew best, generating revenue. Since then, John Sherer wrote an article called “How to take a vacation and still hit your number.” Inspired, I’ve decided to share actionable steps to help you take more vacations while succeeding as #1 on their company’s sales roster.

Defeated, I requested a demotion from a Channel Manager role. Failure to quickly scale our partnership program led me to sacrifice my ambition and instead point towards studying basic sales principles. After a decade of this stuff, I re-embarked on my Account Executive journey to balance my life with a diligent ambition to raise the bar. I knew I needed to improve not only to keep my job but also to be my best self.

In that time, I’ve learned a lot. So without further ado, here are 14 actionable steps to take more vacations while still crushing your sales quota.

Step 1: Identifying a true north.

Last December, I watched the personification of my true north push boundaries on the sales floor. His name is Josh Gillespie. He’s been with PandaDoc for four years. He was the #1 rep who closed over $520k in 2016. He solved everything. Confident and articulate, his clients adored him.

I, on the other hand, was a newcomer, vulnerable, incomprehensible; in short, I sucked. My instinct was to bookmark his dashboard. I had 12 months to echo a stellar performance.

Step 2: Know your worth.

Obsess over dashboard activities. Exploit performance indicators and be your own boss.

Control the number of calls you dial, the number of emails you send and the number of meetings you set, daily. Backdoor calls are supreme to closing deals on the spot. You are a timeline of your activities. Taking long breaks, chit-chatting or intentionally out-working, your esteemed colleagues is a reflection of grit. Know your worth.

Step 3: Double Down.

Let’s say you closed $200k for your company and worked an average of 15 hours per week on meetings, emails, and phone calls. Your activities are generating $3,846 per week.

Now imagine this: Double your activity 2x or 3x (30 hours to 60 hours more), which would generate $7,692 per week to $11,538 per week. Produce $11k per week multiplied by 52 weeks, and that is $572k per year.

After all, 15 hours of production per week is a kind of vandalism. Double down.

Step 4: So I creep. Yeah.

Creeping on a sales dashboard is useful when integrated with a calendar.

I divided Josh’s annual revenue by 12 months and created an event in my calendar to hit my number monthly. Assimilate daily quotas, weekly quotas as you would monthly quotas. $44k divided by 20 selling days equal, $2k/day or $10k/week. Include breakdown numbers as events in your end of the day, end of week and end of month calendar.

Step 5: Integrate motivation.

Hard work is in the eye of the beholder. Personal ideals, travel goals united with day-to-day work transforms the perception of ‘work.’ For instance, invite your friends to a breakfast event. Meetings can also be applied to friends and family. Scheduled from 6am-8am, create a detailed checklist inside of each event vetting best flights, hotels, and destinations. Planning your next trip with your best friend is motivation, and it gears you up for the next work meeting. Also, travel tips are fantastic icebreakers.

Step 6: Calendar gamification.

Schedule rewarding events on the 1st of the month or the first weekend. At the beginning of the month, I always go to the barber to get a nice taper fade and celebrate the new month with my wife. Mental hacks are vital to keeping yourself from burning out. Gamify your calendar with rewards, and you’ll begin to perceive every event as a reward.

Step 7: Travel match.

Similar to 401K match, invest income margins in a travel fund. Call your bank and open a checking account specifically for travel expenses. Juxtapose paying your bills by funding your travel account. For example, if you pay $100 for a phone bill, put $100 in your travel fund account.

If that’s too much work, just download Qapital. Qapital is a new way to bank that lets you save for the stuff you want, only by doing the things you do. The app allows you to set up savings “Goals.” Customize rules to help automate individual savings goals. It’s fun and mindless.

Step 8: Iterate or irate.

Many reps point fingers when they don’t hit their numbers; even I’m guilty of this. Some even throw silent tantrums. Closing $44k per month requires iteration, not irritation. The first three months (Q12017) as AE, I studied Josh’s calls, recorded his demos, transcribed his pitch (from pauses to tones and even vernaculars).

Though I made some unreasonable complications, I took zero vacations and used Josh’s script for three months. Showing up and shutting up, I mindfully held onto conniption fits and instead requested guidance.

As if I were not already annoying enough, I asked Josh to record a training video. Can you guess what the topic was? Knowing your worth. Discover more here. Iterating is your unfair advantage.

Step 9: Mini-Holi-PTO

Studying is stressful. Schedule a short 5-day vacation to avoid exhaustion. Request a paid time off (PTO) before and after a holiday to optimize paid days. At your mini-vacation, use your travel fund (from Step 3) to purchase your flight 3 months in advance. Look at your holiday calendar and request your next PTO today.

Company events will always come up, and if you don’t schedule your vacation 3-6 months in advance, PTOs will get pushed to the back burner.

Step 10: Obiter dictum.

To beat Josh’s monster number, I redefined my goals at the end of May. To do this, I required a surplus of advice. I spoke to managers, top reps and even met with my VP of Sales, Jared Fuller. Together we figured that I had to accomplish the following to be like Josh:

Step 11: A team that vacays together, sticks together.

Go on mini vacation with your leader. Last year, PandaDoc flew our best reps Josh, Will, and Emily to Minsk, which led to mini trips around Europe. They crushed their number. Their teamwork and camaraderie inspired me to travel more with those I look up to. Earlier this year, I invited Josh to my destination wedding in the Caribbean. We spent a lot of time discussing strategy, mindsets, and motivations – we shared tactics in Aruba while enjoying a pint of beer.

Step 12: #Teamnosleep.

Work after hours and weekends, every other day – together. Accommodate it. I’m working after hours on a Sunday night now – and so is Josh. Work is fun when you’re not alone. The privilege of receiving additional training, insights, and hacks that no one else is learning is another competitive advantage.

Step 13: Read your employee handbook.

Our handbook states, “Regular full-time employees are those normally scheduled to work and who do work a schedule of 40 hours per week. Your manager will assign your individual work schedule and will from time to time assign hours outside of normal business hours.” Wisely work remotely as a globetrotter.

Since most tech companies are global, we are allowed to work international hours. Timezone is like an elbow room when lining up your vacation. Request to work 3 pm GMT – 10 pm GMT (which is 8 am PST – 3 pm PST) to continue your routine. To break records, work on vacation. Closing deals on vacation is a better buzz than a shot of tequila. It’s intoxicating!

Step 14: Sales boot camp.

Do not conform to mediocrity. I was fortunate enough to have a leadership team that invests in our professional journey. Earlier this year, Richard Harris led our sales team through a Sales Training Boot Camp A day of tailored training, and a series of actionable next steps were set in motion to help each rep excel. For six months, this playbook and my meetings were inseparable. Sidestep your sales training, and you’re doomed to mediocrity. At the very least, reach out to Richard and inquire about his sales methodologies. Eagerness to learn results in inevitable transformation – applicable to anything in life.

The Harris Consulting Group provides real-world examples to help build sales manuscripts. He does not tell you what to do, instead teaches you how to hit your numbers with simple, practical and real-world exercises.

Step 15: Millennials <3 Texting

Texting is in. Some fear it. I embrace it. Above you’ll see different types of text messaging use cases. The left is a reminder because the client was late to a meeting. As an extension to Google Calendar invites or emails, use text messaging as a platform to communicate.

Follow-up is another use case to move the needle forward. 44% of salespeople give up after one follow-up. The text discussion on the right is my inability to give-up because the prospect is going dark. He wasn’t responding to several calls, voicemails, emails and so I had to use the all-mighty text routine. Notice after three days he finally responds.

80% of sales require five follow-ups. Below you’ll find a slew of text messages enabling me to close a $17k deal. Rapport is the only caveat to bear in mind. Use laughter as your metric to send a text. During a call, if your prospect engages with jokes and casual chit-chat, then you have earned the right to send a text. The text conversation below is how I overcame objections while the prospect, who was a champion, guided the decision maker to sign on the dotted line.

I’m not well-versed on our API/SDK so entailing an engineer is a necessity. Further, our software is updated every week, and a boatload of particulars are published incessantly. Likewise, every client encompasses unique scopes, nomenclatures, processes, and nuances. Requesting reinforcement from a manager, account manager, customer support, engineer, marketing is key to opening doors to happy clientele.

Above is our Technical Manager James hopping on a live closing-call after I’ve solicited support in our Slack channel. Without surveying a particular product merge from Nutshell CRM to PandaDoc documents, the client didn’t feel comfortable signing a $10k deal. James vaulted in, tweaked our flow, enabled a function and bam! The client signed on the spot.

Sitting at the Blue Lagoon in Iceland, I wonder if anyone will do these basic steps. I’ve blogged before, but I’m not aware of anyone applying anything I’ve shared. Like records, goals are meant to be shattered. Nine months ago the quest to close $521k in 12 months seemed impossible. Today, I’m humbled that with Josh’s guidance and two vacations this year, I’m on pace to hit and break the record. Three more months to end the year, I’m holding myself publicly accountable to finish the year strong.

In closing…

Imagine scaling this way of life. A sales life where we travel, work on a beach, close a deal and go scuba diving soon after. Imagine if every rep elevated themselves to extraordinary heights. The company wins, you win, and your friends and family win (you get to kick it more often).

It’s 2017. Scaling an ideal lifestyle is an extension to generating revenue. So put on your positive pants and leave Negative Nancy at the door. I challenge you to complete just one of the actionable steps above. If you’re feeling adventurous, choose three, but do them now sans hesitation. I’m keen to hear your stories of success – comment with them below.

Zen Cachola

Zen is an Enterprise Sales Rep at PandaDoc. Every day she works with large organizations to educate them on our proposal software tool. When she's not pounding the phones or doing demo after demo, she enjoys meditating in deprivation tanks, practicing yoga and savoring freshly squeezed honey ginger lemon apple juice. Connect with her https://www.linkedin.com/in/zenlenon